Dave Chappelle Discusses How He Met The Roots & His First Encounter With Kanye West On The Tonight Show

Dave Chappelle took to yet another late-night program when he hit The Tonight Show to rap with Jimmy Fallon about some of his more elite showbiz homies, how the years have been treating him and — most importantly — his upcoming 9-night sprint at Radio City Music Hall. Following up a humbling and revealing appearance on David Letterman earlier in the week, the natural explained his absence from social media — stalking and tormenting fake Chappelle accounts, resulting in some catfishing of his own with Katt Williams — how he spends time with his kids (Pacqiao fights anyone?) and how much more famous Fallon has gotten in the years since his departure from the limelight.

Once all that was out of the way, Chappelle adamantly proclaimed that “Dave Chappelle loves music” and jumped into how he met The Roots crew for the first time — catching their show in Portland, ME after being mistaken for a “lost Root” in a shopping mall just before — jumping off a long and meaningful friendship as well as cementing himself into the crew. Chappelle’s excursions with the crew led him into the madness of an early 2000’s Electric Lady Studios when Questlove, D’Angelo, J Dilla, Erykah Badu, Common, Bilal and so many more took up residency in the shrine that Jimi built to craft their own masterpieces.

After a brief window into those foundational moments of the Soulquarian movement, Chappelle touched on that one time Prince judo-ed his impression into a bonafide cover for his single “Breakfast Can Wait” and how he knew Kanye West was going to be a star from the get-go, essentially witnessing the birth of Yeezus while looking over footage from his show with Common, Talib Kweliand ‘Ye himself. After comparing Kanye’s demeanor to Ali in the Olympic Village, Chappelle described a scenario where The four of them were listening to JayZ’s Black Album and Hov opened up “Lucifer” with some shine for West — and some surprising shade for Common — evoking a standard Yeezy response : “Stop the record and rewind that!” West’s ascension into Yeezus-status came as he picked up the phone mid-editing session and explained to the individual on the other end that he was watching skits from Dave’s show that nobody had ever seen, explaining “’cause my life is dope and I do dope shit” as he hangs up the phone. For all of these stories and more head down below to watch both parts of Chappelle’s hilarious appearance on The Tonight Show and get reacquainted with the genius of our resurgent king of comedy ahead of his Radio City run next week, where he’ll be reuniting with the Block Party crew.